Steve Gerald on Carrying Herman Woodcrafting’s 40-Year Legacy Forward in Southwest Florida

Some business stories begin with a carefully planned career path. Steve Gerald’s began with a return home.

Before becoming the co-owner and day-to-day leader of Herman Woodcrafting, Steve was a Fort Myers kid who grew up around the beaches, neighborhoods, construction sites, and service businesses of Southwest Florida.

He graduated from Cypress Lake High School, earned an associate degree from Edison Community College, and eventually joined the U.S. Army. His military service exposed him to communications technology, computer-based operations, overseas assignments, and leadership responsibilities at a relatively young age.

After leaving the service, Steve returned to Southwest Florida with a clearer sense of what he wanted to build. He enrolled at Florida Gulf Coast University, studied computer science, and began working more closely with his father, John Herman, at the family business.

During our SWFL Spotlight interview at MelloD Designs, Steve’s story repeatedly returned to three themes: adaptability, responsibility, and service. Those values have helped Herman Woodcrafting survive changing construction markets, maintain relationships that span decades, and begin preparing a new generation to carry the craft forward.

roots and early work

The Person Behind the Business

Steve’s connection to construction began long before he considered it a career. He started working around age 13, cleaning construction sites for a friend’s father in San Carlos Park. The work involved sweeping, collecting scrap lumber, and clearing debris from active job sites. It was not carpentry yet, but it was his first exposure to the building industry.

As a teenager and young adult, Steve worked at Moss Marina on Fort Myers Beach, where he drove a forklift and helped serve boaters visiting the area. He later worked as a doorman at the Ritz-Carlton, an experience he credits with helping him understand customer service. Meeting people as they arrived, anticipating what they needed, and making them feel taken care of left an impression.

“I really feel like that’s when I got my taste for service,” Steve said.

That service mentality would eventually become an important part of the way he approaches construction clients, builders, homeowners, and employees.

Steve did not initially plan to become a carpenter. After earning his associate degree, he entered the Army and pursued opportunities involving aviation, communications, computer systems, and field operations. His military experience required him to adapt quickly. At one point, he was responsible for moving soldiers and equipment through Europe and connecting with an operating base in Hungary. He was still in his twenties.

The experience taught him to take responsibility, coordinate people and equipment, solve problems under pressure, and step into leadership when leadership was needed. Those skills followed him home.

After completing his military service, Steve enrolled at FGCU and earned a degree in computer science. He described himself as part of the university’s first full graduating class to complete its computer science program in 2000. While attending college, he worked flexible hours for Herman Woodcrafting, taking mornings, afternoons, Saturdays, and whenever his class schedule allowed. That was when he began learning the craft in earnest.

Steve learned the different facets of trim carpentry from his father, including the standards required to work inside professionally built homes. He is quick to credit John as the stronger hands-on carpenter and stair installer. Steve found his own strength in management.

“My dad is an excellent carpenter. I’m a better manager, I think, than he is. But we’re a good fit together.”

Steve Gerald

why the family business

Why He Chose the Family Business

Steve’s decision to join Herman Woodcrafting was about more than having a job waiting for him. While serving in the military, he met the woman he wanted to marry. He knew he wanted to bring her home to Fort Myers and build a life near his family. The family business provided a foundation.

Steve could earn his way through college, learn a skilled trade, and gradually take on more responsibility as his father approached retirement age. The transition was not a traditional corporate handoff. Steve describes the company as a partnership in which John remains involved at the level that works for him.

“As long as he wants to be contributing to the company, I’ll find a spot for him,” Steve said.

Steve hopes the same kind of flexibility will eventually be available to him. His son has started learning the trade, working in the field, and gaining exposure to the company’s management and technology. Still, Steve does not assume that his son must follow the same path.

“He’s not me,” Steve said. “He’s got to choose his own path and make sure that it’s a good fit for him.”

Steve would be proud to see the business continue into another generation, but his larger goal is not simply to preserve his own position.

“I want him to exceed me.”

Steve Gerald

surviving the downturn

Building a Business That Could Survive Change

Herman Woodcrafting’s longevity has required more than technical skill. At its height before the 2008 housing downturn, the company had approximately 25 carpenters, three field supervisors, and a four-person office team operating from a brick-and-mortar location.

When Southwest Florida’s housing market collapsed, that structure became impossible to maintain. Steve had to let go of most of the company’s carpenters, office employees, and supervisors. The business contracted to a small core team, and Steve temporarily left to drive a truck and take computer-related work wherever he could find it.

The company survived, but it did not return with the same operating model. Steve and John adapted. Today, Herman Woodcrafting combines experienced hourly employees with specialized subcontractors. This allows the company to expand or contract according to the volume of available work while maintaining direct oversight at the most critical stages of each project.

Steve keeps his employees involved in the beginning and end of projects, where preparation, quality control, corrections, and final details can have the greatest effect on the customer’s experience. The model also allows Herman Woodcrafting to serve a large territory without maintaining the same overhead it carried before the recession.

“We changed our model,” Steve explained. “It allows us to be competitive and flex up and down in size as the market expands.”

at home in southwest florida

Building in Southwest Florida

For Steve, Southwest Florida is not simply a service area. It is home. He grew up in Fort Myers, spent time on Fort Myers Beach, attended local schools, and watched the region change from a smaller coastal community into one of Florida’s fastest-growing areas.

He has also watched local design preferences evolve. Homes that once emphasized ornate columns, decorative spirals, fluted casing, rosettes, and Tuscan-inspired finishes are now being updated with taller baseboards, smooth flat-stock trim, decorative beams, tongue-and-groove ceilings, clean stair systems, and modern coastal styling.

Some of the company’s work has come full circle. Steve occasionally receives calls about homes Herman Woodcrafting originally trimmed 20 or 25 years ago. The houses are still standing, but the owners want a different look. Herman Woodcrafting may replace narrow baseboards with taller profiles, update door casing, remove outdated decorative elements, install modern stair components, or add accent walls and beams.

Because most of the work is decorative rather than structural, homeowners can make a noticeable change without completely rebuilding the home. Steve describes Herman Woodcrafting as an underused resource for individual homeowners. The company has traditionally worked directly for builders, which means many residents may not realize they can hire the same type of professional trim company to update an existing home.

The company’s footprint extends from Marco Island to Port Charlotte and west toward Sanibel. Its long-term builder relationships have kept the business moving from community to community, often through word-of-mouth referrals and repeat opportunities. Steve said Herman Woodcrafting has worked with some builders for 25 to 30 years. Those relationships reflect the value of reliability in the construction industry.

“You typically contract with the people that you trust. For us, having 40 years’ worth of experience, we have that trust built in.”

Steve Gerald

the full scope of the work

More Than Doors and Baseboards

The term “trim carpentry” can sound narrow, but Herman Woodcrafting’s work extends through many of the finished wood elements inside a home. The company installs interior and exterior doors, door casing, baseboards, window trim, crown molding, cabinets, decorative wall treatments, handrails, stair treads, newel posts, balusters, barn doors, beams, tongue-and-groove ceilings, and specialized hardware.

“If it’s wood inside your house, I can install it.”

Steve Gerald

The company also installs decorative trends homeowners may discover through model homes, magazines, Pinterest, Instagram, or TikTok. These can include board-and-batten walls, geometric accent patterns, vertical slat walls, ceiling beams, and other applied wood features.

Decorative beams are one example of how trim carpentry can transform a room quickly. Although the finished product may look like a large solid timber, the beam may actually be assembled from several lighter pieces of lumber. Steve’s team constructs and installs the pieces to create the appearance of a substantial beam without adding the weight or complexity of a structural timber.

“People leave in the morning, they come back in the afternoon, and it looks like there are giant, massive beams in their living room,” he said.

That kind of transformation reflects what experienced finish carpenters do best: create details that make a completed space feel intentional.

behind each installation

What Customers May Not See

Behind each installation is a significant amount of scheduling, estimating, coordination, and quality control. Steve personally manages much of the company’s pricing, billing, and scheduling. He works to control costs closely enough to remain competitive while accounting for labor, insurance, transportation, materials, and the logistics of covering a large geographic area.

His background in computer science and military technology also influenced how he modernized the business. As early as 2006, Steve was experimenting with convertible tablets that allowed field employees to record notes, prepare quality-assurance lists, and complete job reports electronically. Today, the company uses a digital platform for scheduling installations, forecasting upcoming work, sharing information, and coordinating projects.

Steve believes Herman Woodcrafting may be one of the more technologically integrated trim carpentry companies in the region. His son is also helping the business explore newer tools, including AI-assisted visual concepts that can show homeowners how a stairway, ceiling, exterior door, or decorative feature could look before installation.

Technology helps with organization, but Steve believes responsiveness still matters just as much. He returns phone calls. He looks for ways to help builders solve unusual problems. He answers requests that other companies may ignore, including work that arrives at inconvenient times. He recalled how being willing to work on a day such as Christmas Eve could create future opportunities because customers remember who answered when they needed help.

“If we can’t do it, I’ll tell them,” he said. “But most times, we can.”

That responsibility extends to the people who work for him. Steve knows the business supports more than his immediate family. It also supports employees who have worked with Herman Woodcrafting for 20 years or longer, along with their spouses and children. During difficult periods, Steve said he has personally gone without a paycheck to ensure his employees were paid.

“I’ve gone without pay to make sure that my people got paid.”

Steve Gerald

That willingness to absorb pressure is one of the clearest examples of how Steve views leadership. When the company succeeds, he accepts responsibility. When something goes wrong, he accepts that responsibility too.

training what comes next

Passing the Craft to the Next Generation

Herman Woodcrafting is currently looking toward another period of growth. Steve shared that increased workload has created a need to recruit additional carpenters. He is open to experienced applicants, but he is also willing to train people who demonstrate aptitude, reliability, and a willingness to learn.

In some cases, he prefers applicants without extensive experience because they can learn the company’s methods without first having to unlearn habits developed elsewhere. Certain fundamentals are required. Applicants need to be able to read a tape measure, hold a driver’s license, operate a vehicle, and work safely around tools and job sites. The rest can be taught.

Steve sees trim carpentry as more than a position with one company. It is a portable skill someone can use throughout a lifetime.

“If you learn how to do this job, you could literally work anywhere.”

Steve Gerald

Over the years, carpenters who started with Herman Woodcrafting have gone on to become cabinet installers, general contractors, builders, and business owners. Steve does not view that entirely as a loss. Teaching someone to examine work critically, meet a high standard, and deliver a finished product that customers will accept gives that person a foundation for future opportunities.

He also recognizes that fewer young people are entering skilled trades. The number of people who know how to finish drywall, perform electrical work, install trim, or complete other specialized construction tasks is shrinking. By teaching new carpenters, Steve hopes to protect not only the future of Herman Woodcrafting but also the future of the trade itself.

“I want to train the next generation of young people who may be looking for a trade,” he said.

about the business

About the Business

Herman Woodcrafting is a trim and finish carpentry company that has served Southwest Florida for approximately 40 years, working for homebuilders, contractors, developers, and individual homeowners. The company installs and updates the finished wood elements throughout a home, including:

• Interior and exterior door installation
• Baseboards, door and window casing, and crown molding
• Stair systems, handrails, newel posts, and balusters
• Decorative beams and tongue-and-groove ceilings
• Accent walls, barn doors, cabinets, and hardware installation
• Whole-home trim updates and other decorative wood features

Herman Woodcrafting serves Marco Island, Naples, Bonita Springs, Fort Myers, Sanibel, Cape Coral, Port Charlotte, and surrounding Southwest Florida communities. The business can be reached at 239-433-2600 or online at HermanWoodcrafting.com.